My Favorite Mistake
by Razorbackgal0225
Summary: Complete and total fluff, starring my favorite Winchester boy, Dean.  What exactly happens when Dean picks up a girl?  And what happens when it’s not the type of girl who normally says yes?  Please read and review!
1. Chapter 1

Title: My Favorite Mistake

Author: Razorbackgal0225

Rating: M—For language, sexual situations and nudity. Three of my favorites

Disclaimer: I don't own any of the characters, cars or situations from Supernatural, but I sure wish I did. Anything you recognize doesn't belong to me, including the title which comes from a Sheryl Crow song. Other songs included in the story are from the group Heart and Pat Benetar. I made no money off anything, I swear!!

Author's Note: For those who have read my other stories, this has absolutely nothing to do with them. This is just something that was running around in my head, screaming and refusing to rest until it was written down. So here it is, my first and I do mean first attempt at what I affectionately call smut. I have no experience with this, so please be gentle. This will be fairly short, only a couple of chapters and I am still working on Catherine's Shack. Enjoy!

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She noticed him as soon as he walked in the door. Of course, she had the best view of the entrance, being on stage singing. Generally she didn't notice who came in or went out of the bar as she was concentrating on lyrics, but this guy was different. First of all, she didn't recognize him, which was odd. This was a bar frequented by regulars as it was off the beaten path and away from the other roadhouses on the interstate. Second, the guy he was with was about three inches taller than anyone in the room, which drew some attention. Last and most importantly, he was brutally hot. Not that normal pretty boy look that some of the frat guys from the next town over had, the ones that spent too much time on their hair. This was plain ole, purebred, he'd-look-good-in-a-potato sack sexy. So much so that she had to wrack her brains for which verse of "Magic Man" she was on. 

He sauntered up to the bar; the tall guy going to find a table about 10 feet from the stage as he did. She tried to not stare at him as he walked across the floor, but couldn't stop herself. She noticed several other girls turn to do the same. He was dressed simply enough, in jeans, t-shirt and button down shirt over it. The sleeves were rolled back, showing strong forearms and wrists and tan skin. The shirt stretched over broad shoulders. His brown hair was cut short and he looked like he hadn't shaved since the morning before. He took two bottles from the bartender and joined his friend at the table. He positioned his chair so that he could see the stage and the door at the same time, just as her dad did when he came to see her sing. She knew from the glance she had got when he came in that he was good-looking, but that didn't prepare her for an up-close and personal view, when he turned to face her.

He was absolutely gorgeous. Golden skin, a strong jaw line, hazel eyes, sinfully long eyelashes and a mouth that should be labeled as illegal. His friend was cute as well, but she barely noticed. Thankfully it was time for her next song, so she had an excuse to turn her attention to the band. When she replaced the mike in its stand, she noticed he was watching her. Listening to the intro of 'Hit Me With Your Best Shot' playing, she picked a spot on the back wall to sing to, hoping that would keep her from being distracted. It didn't work. She kept looking back at him, and every time she did, he met her gaze. Even when his friend spoke to him, his eyes didn't leave her. When she reached the part about notches on a lipstick case, he smiled. And her mouth went dry.

His smile was full of heat, promise and sin. The smile reached up to his eyes, the same eyes that were giving her an extremely appraising look. He was exactly the sort of guy her momma had warned her about. Her heartbeat kicked up a notch and she was glad she was on the last song of the set. He was coming dangerously close to causing the reconsideration of her 'never pick up a guy at a bar' rule. Something no guy had done in a long, long time.

She finished her song, waved to the crowd and helped the band tear down for a few minutes. Then she headed to the bar for her traditional after performance beer. She grinned at the bartender, who had the bottle waiting on her before she even sat down on the stool. She was halfway through with her drink when she felt someone come up beside her. She didn't even have to turn around to see who it was, since her stomach started backflipping the minute he approached.

"Can a get another one?" his deep, slightly rough voice washed over her like a wave on the beach. It wasn't fair that men could sound that hot. Out of the corner of her eye, she saw him place a hand on the bar as he turned slightly in her direction. Unable to stop herself, she tilted her a little to get a better view.

The smile was still there. She took another drink of beer, swallowing nervously as she did. She saw him make another gesture to the bartender and was surprised when Pete placed another bottle in front of her. That did it. She couldn't ignore him any longer, no matter how much she should avoid the temptation. "You don't have to do that," she said quietly.

"I know," came the answer. This time, she focused on him completely. He lifted the bottle to his mouth and she wished she could temporarily be made of glass. "But after a show like that, I thought you deserved a drink," he explained after swallowing.

She frowned slightly. "But you only saw two songs," she said.

The smile grew to a full-blown smirk. "So you noticed me?" he asked, although it was more of a statement of fact than a question. She ducked her head, a light blush spreading across her cheeks. This only lasted a minute, before she met his eyes again.

"I know everyone else in here," she answered, gesturing around the room. "You're a new face."

He lowered his body onto the barstool next to her. "I'm Dean," he said, holding out his hand.

She waited a good five seconds before placing her hand in his. "I'm Madeline."

As a rule, handshakes didn't turn her on. But when his strong, warm hand clasped around her much smaller, she couldn't help but notice, one, her breath caught in her throat. It didn't help that he held on longer than socially acceptable or that he ran his thumb over the back of her hand. The warning bells in her brain started ringing loudly and she slowly extricated herself from his grip. This was beginning to feel like a pick-up, and she didn't know if she could say no. Maybe she should have gotten her beer to go.

"You really do have a great voice," he commented, scooting his chair closer to hers. "Is this what you do for a living?"

Uh-oh, step #2 in the picking up process. Compliments. She pushed a strand of hair out of her eyes before she replied, "No, I just do this for fun. I'm not nearly good enough to do this for real." She finished her first beer. She hated to drink in a hurry, but she needed to get out fast.

"Really?" His voice was filled with genuine disbelief. "You sounded good enough to me. Anyone that can sing Heart has my vote."

She laughed. "Well, if I ever need a reference, I'll be sure to send them your way." Three more sips and you're leaving, she told herself.

"What do you do when you're not singing?" he asked.

"I work at the bank in town. What about you? What brings you here of all places?" Okay, maybe four more sips.

He jerked his head towards the guy still sitting at the table. He was flipping through a notebook of some sort, oblivious to everything around him. "My brother and I are on this bonding, road-trip kind of thing. We just stumbled upon this place and thought it looked interesting."

"So is it?" The question left her mouth before she had fully processed what it sounded like. One day, she would learn to think before speaking. Like that hadn't sounded like an open invitation.

She risked glancing at him when he answered. "Oh, I don't think interesting is quite the word I'd use." The grin was back and causing her to flush in places that weren't polite to mention in public. Damn it, she had to leave now before she did something extremely foolish. Like staring into his eyes, as she was doing right now.

His eyes were beautiful, she decided. And filled with heat and lust and the promise of an extremely good time. A promise she was fairly certain he could deliver on, in spades, but unfortunately, she just wasn't that kind of girl. So she did the only sensible thing she could do.

"Thanks for the drink, I appreciate it," she said, sliding to the floor as she did. "I've got an busy day tomorrow, so I'd better get going." She almost cringed at how obvious her brush-off sounded, but she was in flight mode now.

He frowned slightly at her announcement, then stood as well. "Let me walk you to your car, then."

She paused a minute before replying, "That's alright. I actually live two blocks down, so I walked here. It was nice to meet you, Dean." She hated being borderline rude, but this was about self-preservation.

He threw a few dollars on the bar before following her. "You're going to walk home alone at this time of night?" he asked, rather reproachfully. "Let me tell Sam where I'm going and then I'll walk you home."

She opened her mouth to protest, completely sure she was capable of getting home. But when she saw the look on his face, one of actual concern for her safety, she melted a little. He didn't know that she had lived in this town all her life. He didn't know she had every crack, bump and split in the sidewalks of the city memorized. He also didn't know that with the mysterious disappearances that had happened lately, she had taken to carrying a gun in her purse. Either he was really worried, or he was a fantastic actor. So she silenced her protests and turned off the warning bells in her head for a few minutes.

When he saw that she didn't disagree with his idea, he walked quickly to his brother. After a small discussion, he smacked the other man on the back and returned to where Madeline was waiting.

They silently left the bar. He walked close enough to her that their arms brushed as they made their way down the sidewalk. Madeline didn't have any idea what to say to him, so she chose to not say anything. It took about five minutes to reach her house. At the front gate, she stopped.

"This is me," she said, placing her hand on the gate. As she started to push it open, he placed a hand on top of hers. She looked down, surprised by this action. He took that opportunity to step closer to her until only inches separated them. His thumb resumed the suggestive stroking on her suddenly sensitive skin. He used his other hand to gently push her hair behind her ear, then ran his finger along her jaw. She looked at his eyes, which had darkened in the last few minutes, and were now a deep brown. He was staring at her mouth.

"So, this is goodnight?" His question was loaded with meaning. Every silly, feminine part of her was shouting for her to answer 'No, no, no, don't go, don't go!' But the sensible, grounded, common sense part of her knew this was not the best idea. Her two halves warred for a minute and she finally answered.

"Look, it's not that you're not extremely tempting, because, trust me, you are. But I'm really not that kind…" her response was effectively stopped by his lips covering hers. The devil on her shoulder gave a standing ovation. The angel on the opposite sat and pouted. His hand that had been resting on hers moved to the small of her back. The other took up residence on her neck, tugging on her hair enough that she had to tilt her head back. He tasted of beer and danger, a heady combination. His lips moved confidently over hers, as his tongue began a delightfully thorough exploration of her mouth. Her arms, of their own accord of course, lifted and wound around his neck, pulling him even closer to her. He groaned, a sound she felt more than heard, and deepened the kiss. The devil started the wave.

He slowly ended the kiss, giving her lower lip a nibble as he did. For a few seconds, Madeline tried to remember where she was and what her name was, but failed miserably. "I'm sorry, what were you saying?" he whispered, his mouth now having moved to her ear. His lips brushed the shell of her ear and she shivered. She was fairly certain she had been talking before he had kissed her, but she couldn't remember what it was. Oh yeah, she was going to say she didn't do this sort of thing. As he continued on his journey down to her neck, she finally harnessed her thoughts.

"I'm not really that kind of girl," a decidedly breathy voice that sounded nothing like her answered. Her statement wasn't very convincing, especially when followed by a gasp as Dean grazed her neck with his teeth, before soothing the skin with his tongue.

"I know," he murmured against her skin. Her hands gripped his shoulders reflexively as the vibrations from his words ran through her. It had been forever and a day since a guy had affected her like this. He lifted his head and suggested, "Maybe we could go in and I could try and convince to change." He followed this with another slow, drugging kiss. The devil jumped to the other shoulder and kicked the angel's ass.

He deftly used the hand that wasn't holding her up to unlatch the gate and started guiding her to her front door. All this while still kissing her. She was surprised she could walk on her own, much less find her keys in her purse and unlock the door, as his busy mouth had returned to her neck by this time. The man certainly had talent. She pushed the door open and he followed her inside.

Two seconds later, she found herself pinned to the wall by six foot of solid muscle. For about half a heartbeat, she reconsidered her decision, seeing as how he was a complete stranger. That didn't last long. He continued his assault on her mouth, one she eagerly welcomed. His hands began to roam over her body, lighting fires that had long been dormant. They finally rested on her breasts, his thumbs circling tantalizingly around her nipples. She whimpered in the back of her throat and arched her back, encouraging more contact. He smiled against her mouth and gave her what she wanted. The pressure he applied to the tips of her breast shot sent an electric current from her head to her toes. She moaned and gripped his shoulders even harder than before. Her nipples quickly grew hard and aching as he worked them.

Her hands skimmed down his arms and went on search of her own. She tugged the hem of his t-shirt up and was rewarded with warm, silky flesh. In the corner of her mind that was still working, she was surprised how soft his skin was. The muscles of his stomach clenched and tightened as she stroked him. Suddenly, her hand was trapped between them when he released her breasts and pulled her body flush with his. She gasped and he growled when his hard planes met her soft curves. With one roll of his hips, she was tearing her mouth away from his to breath, as the evidence of his arousal was pressed against her cleft. He buried his head in her neck, biting softly as he did.

"Oh, God, please tell me I can stay," his plea was ripped from deep in his chest. The chest that felt like iron against hers. He ran his hands down her side and grabbed her ass, picking her up slightly as he did. This caused her to reflexively wrap her legs around his waist. Now she was supported by only the wall behind her and Dean. "Please," he reiterated. Madeline shook her head in response before he took her mouth again. The movements of his tongue now matched the movements of hips, thrusting at the same time. All of the sensations were causing bells to ring in her ears. Except that the ringing wasn't in her ears.

"Fuck," he muttered as his mouth left hers. Still supporting her, he reached into his back pocket and brought out his cell phone. He glanced at the caller ID and cursed again, "Fuck, Sam." He threw an apologetic look at Madeline and answered harshly. "What do you want Sam?" Since she only heard half the conversation, she had no idea what was going on, but it didn't sound good. "You're kidding, right now? Well, I'm kind of in the middle…" his explanation trailed off. "Alright, alright, I'll be there." Hearing that, she unwound her legs from around him and began to right herself. Letting go of her for the first time since they left the bar, he scrubbed a hand across his face and then his hair. "I'm sorry, baby, I've got to go. Something's going on with my brother." He smiled sadly at her. "I really, really wish I didn't have to go."

She swallowed hard, wanting to regain her bearings. "No, that's okay. He's your brother," she agreed, pushing her hair out of her face nervously. He reached up and dragged his thumb across her mouth. Her lips parted behind this action and it as all she could do to not lick him. He stroked her cheek tenderly and leaned in for another kiss. It was soft and sweet, nothing like the ravenous, hungry kissed from before.

"Maybe, if I wrap this up, maybe I could come back?" he asked shyly, his tone quite at odds with his aggressive actions from before. She paused for a minute, unsure of what she should say. "If it's not too late, that is. I know you have a busy day tomorrow." He grinned at her, remembering her excuse earlier. She laughed at herself and smiled back.

"Yeah, that would be alright." This response gained her another kiss.

"Okay. I'll do everything I can to be back, I promise," one more peck on the cheek and a brush across her breast and he was out the front door.

Madeline gave up standing on her own and slid down the floor. Covering her eyes with her hands, she concentrated on breathing evenly. Even if he didn't come back, she would remember this night for a long time. Plenty of fantasies had been born in the last hour. She finally rose from her seat and headed to the bedroom. Maybe she could get a little sleep tonight. Her skin flushed as she recalled the feel of his hands on her body. Okay, maybe there would be no sleep.


	2. Chapter 2

Title: My Favorite Mistake

Author: Razorbackgal0225

Rating: M—For language, sexual situations and nudity. Three of my favorites

Disclaimer: I don't own any of the characters, cars or situations from Supernatural, but I sure wish I did. Anything you recognize doesn't belong to me, including the title which comes from a Sheryl Crow song. Other songs included in the story are from the group Heart and Pat Benetar. I made no money off anything, I swear!!

Author's Note: Consider yourself warned, you are about to enter adults only territory. If this type of story offends you or is not your cup of tea, I recommend leaving now. For the rest of you, sit back and enjoy the ride. At least, I hope you do :-) Let me know what you think.

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The knock on the door woke Madeline from her light sleep. She checked the clock and saw that it was 2:00. That meant she had been sleep for approximately 30 minutes. It had not been easy to calm down after Dean had left, and then she had been half-worried, half-hoping he would return. At 1:00 she had finally given up and gone to bed, only to lie awake for a while, reliving the events from earlier. Events that made it extremely hard to fall asleep. She climbed out of bed and flicked on the light in the hall as she passed the switch. She recognized the silhouette on the other side of the glass door, so she slowly opened the door. 

She hadn't been imagining things; he really was breathtaking. He was down to only his t-shirt and jeans, missing the top shirt he had been wearing before. But that sinful grin was still present, along with a set of lust-filled eyes that raked her from head to toe. She wasn't aware a person's entire body could blush, but she was pretty sure hers accomplished it. She had fretted over a choice of outfit when she had changed for bed, just in case he did come back, and had discovered she had nothing appropriate for this kind of night. She wasn't a ruffles and bows type of girl, so the pajamas she wore consisted of a tank top and shorts. The look on his face reassured her that her choice had been more than adequate.

"Can I come in?" his voice startled from her reverie. She blushed again, realizing she had been staring at him and leaving him on the front step. She nodded, moving from the door to allow him entrance. His forearm grazed across her breasts as he walked by, causing her just recently calmed nipples to bead again. The smirk he gave her told her that the contact had been no accident.

This action brought back one of the fears that had kept her awake. She had absolutely no idea what to say to him now. Earlier, talking hadn't been a priority, but now she didn't know what to do. Should she offer him a drink, a sandwich, a condom? She was in new territory and completely unsure of herself. Thankfully, Dean solved this problem for her by asking,

"You don't happen to have beer, do you? I'm kinda thirsty." She noticed as he ran a hand through his hair that he looked a little tired. Maybe he had changed his mind. Maybe this was a sign that the devil on her shoulder was wrong and basically a big bully for shutting up the angel. Her thoughts must have shown on her face, because he smiled and said, "Do I need to start the convincing process over again? Cause that would be fine. I have no problem throwing myself into my work."

She laughed out loud. She couldn't help it, he was actually funny. "No, I'm good. Sorry, I'm just not used to…" she trailed off sheepishly, not even knowing how to refer to the situation. The smile he gave her was genuine this time, not a smirk or a grin.

"Yeah, I know," he answered. He took two steps towards her, eliminating the space between them. He ran a hand up her arm, leaving goose bumps in his wake, then cupped her chin. He brushed his lips across hers and murmured, "You're doing a great job." When Madeline sighed against his mouth, he kissed her. Slowly, methodically and patiently, he destroyed every reservation she had about what was about to happen. He wrapped his arms around her, holding her tightly. Before she completely lost herself in the sensation, she pushed away from him.

"Beer," she repeated breathlessly, "you said you wanted a beer." She stepped towards the kitchen. A strong hand grasped her wrist, stopping her progress. He tugged slightly, bringing her back into his arms.

"Screw the beer," he growled, "I've got more important things to take care of." With that said, he led her down the hallway of her own house. He glanced in the first room, realized it was the spare and pulled her into the last room in the hall. Her bed was as she left it, sheets thrown back and pillows rumpled. It looked soft and inviting. Before she could finish her next thought, Dean kissed her again, framing her face with his hands. His lips and tongue became the center of her universe. That is until his hands moved down her body and gripped the hem of her tank top. Breaking the kiss for a moment, he pulled upward, forcing her arms up. The shirt flew across the room, landing on the rug next to her window.

Her initial nervousness returned for a moment. While she wasn't ashamed of her body or looks, she had never been entirely comfortable being naked in front of someone new. The look of awe and hunger on his face changed her mind. His gaze alone was enough to cause her breasts to swell, her nipples to harden and her breath catch. Normally her arousal was a process, taking certain activities to happen before her body was ready for serious action. She was genuinely surprised by her reaction; already she was becoming wet.

Her surprise continued when Dean dropped to his knees in front of her. Placing his hands on her hips, he pulled her to him. "C'mere," he commanded. She took a step forward and his lips latched on to her nipple. She gasped out loud and threw her head back. His mouth was warm and his tongue was busy swirling around the tip of her breast. She reflexively combed her fingers through his hair, clutching him even closer to her. His teeth grazed the sensitive skin and she moaned. Through the haze of passion she was in, she heard him chuckle before he returned to his task. He used more strength this time, sucking harder than before, and her knees buckled. He wrapped a supportive arm around her thighs, switched breasts and continued to work her.

She was so focused on the pleasure he was giving her, she failed to notice his fingers stroking higher and higher on her inner thigh. Until the tips of his finger slid under the very edge of her panties. Then her knees completely gave out. Dean stood up, not releasing her, and walked her to the bed. She fell backwards and waited for more. He leaned over her, supporting himself on his hands and returned to her mouth. This time, she was much more active, her tongue sliding into his mouth as soon as his lips met hers. He gave a deep groan of approval and slid his hand across her stomach.

The devil that was operating the video camera from the nightstand clapped when Madeline reached down and pulled Dean's shirt over his shoulders. He stopped kissing her long enough to remove it completely. She ran her hands over the newly bare skin, reveling in the feel of his muscles playing under the warm, toned flesh. His mouth moved down to her neck, as his hand moved underneath her short and panties. His knuckles brushed lightly against her center, causing her to whisper, "Oh, please."

"Please what, darlin'?" he replied. "Please this?" He trailed his tongue up the side of her neck. She shivered. "Please this?" He took her earlobe into his mouth and nibbled gently. She sighed. "Or please this?" Dean suddenly slid one finger inside her. She moaned and almost came from the initial contact. He shifted his weight over her, causing his impressive length to rest on her thigh. They both groaned. "God, baby, you're so hot," he murmured, feeling her muscles clench around his finger.

"More, please, more," she managed to plead. From the way this was going, it wasn't going to take much more to send her over the edge.

He leaned down and bit her neck gently. She arched her back in response. "Sure thing, Maddy." He took his finger out and then slid two into her. He began to slowly move them in and out of her. She screamed his name. He bent over her further, taking one of her nipples in his mouth. Moving his hand faster, he sucked hard. She came unglued. She was so close, nearing her release, when he suddenly stopped.

"I like hearing you yell my name," his statement forced her to pay attention. She saw that he had backed away from her and was stripped off his pants and underwear. His cock sprang free, enticingly hard and impressively large. She swallowed nervously, afraid he might catch her drooling. He gripped the waistband of her shorts and she lifted her hips to help him remove the last layer of clothing between them. She expected him to resume the highly pleasurable activity they had been engaged in prior to his pause. But he didn't. Instead he gently pulled her closer to the edge of the bed, so that her legs were dangling over the side.

"What are you doing?" she asked, confused. She was met with a smirk and a nudge at her thigh, prompting her to spread her legs. He again dropped to his knees, kneeling in front of her. She gave a squeal of surprise. "What are you doing?" Admittedly she wasn't at all experienced in one-night stand protocol, she was sure none of her friends who had them were offered this. This just wasn't normal. "You don't have to…" her protest died as he placed an open-mouthed kiss on her inner thigh.

"I told you," he said, getting nearer and nearer to his goal, "I like hearing you yell my name. I intend on hearing it again." With that, he placed his mouth on her. And she went to straight to heaven. Even the angel was on board now. His tongue dipped inside her, tasting her thoroughly. She gripped the sheets beneath her, grateful for something to hold on to. Her hips began to move against his lips, as her pleasure increased with each thrust of his tongue. When he took her clit between his lips and sucked, she shrieked and wrapped her leg around his back, trying to bring him closer. No guy had ever gotten this reaction from her, especially with this activity.

Her orgasm snuck up on her so fast, she didn't even realize it was there until it happened. One last nibble from Dean and her world exploded. She might have screamed his name, but she wasn't sure. She saw stars, heard bells ringing and almost passed out. He continued lapping at her, but gently now, helping her come down from her high. Her heart rate slowed and her breathing wasn't coming in shallow gasps anymore when he raised his head. The grin he wore was lethal; the lazy smile she gave him in return was satisfied. He stood from his crouch and licked his way back up to meet her eyes.

"Whadda you know, I did make you scream again," he bragged. Madeline took matters into her own hands, reaching up and bringing his mouth down to hers. She kissed him, then moved her hands down his back. His skin was warm and smooth and his muscles moved under her touch. Getting her second wind, she wound her legs through his. She used this to gain momentum and roll him over on his back. He was surprised by this, but continued smiling at her.

"Now it's my turn," she drawled, dipping her head to taste his neck. The angel and the devil hugged each other in celebration. His skin was slightly salty and absolutely delicious. She kissed up his neck to his ear, taking a lobe between her teeth and whispering, "Whatever will I do with you?"

He stroked her back, settling his hands on her waist. "I can think of a few things," he answered, his voice rough with passion. She moved back to his neck, sucking hard enough to leave a mark. He grunted and said, "Or whatever you want to do will be fine." Her teeth scraped along his collarbone, as she drifted down to his chest. She traced the line between his pectorals with her tongue before covering a nipple with her mouth. He was very toned, muscles well defined but not bulky. His body had come from work, not years spent in the gym. Something she was definitely appreciating as she explored her new playground.

She worked his nipples as he had hers, swirling her tongue around the first, then biting lightly. He sucked breath hard through his teeth and she felt his fingers tangle in her hair. Proud of herself of eliciting such a response from such a beautiful man, she continued. Trailing her fingers down his sides and over his abs, her lips followed. She was shocked when his grip on her head tightened a little, enough that she looked up from her work.

"What are you doing?" he asked, repeating the question she had voiced earlier. She smiled prettily.

"I think I'd like to hear you yell my name this time," she answered. She moved further down, facing the end of her journey. His cock was fully erect, bobbing gently with each movement he made. She smoothed her fingers over him gently, causing his hips to buck under her. Madeline then wrapped her hand around him, fingers not quite meeting at the base. She slowly stroked him, reveling in the feel of the velvety skin wrapped what felt like steel. She glanced at Dean and saw his head was thrown back, eyes shut tightly. She lowered her head, placing her lips around the head of his shaft and sucked gently. He growled deep from his chest and his hips left the bed. She placed a restraining hand on his thigh, but didn't remove her mouth. She twirled her tongue around him and took as much of him in her mouth as she could. This time when he groaned, it was her name.

Before she could go any further, he grasped her arm and pulled her away from his cock. "Seriously, I'd be more than happy for you to continue, but if you keep that up, I'm not going to last more than a minute." He flipped her back onto her back, kissing her as he did. "And I want to be inside you when that happens." He left her for a moment, finding his jeans on the floor. She propped herself up on her elbows and saw that he was extracting a condom from his pocket. She watched with eager eyes as he opened the packet and rolled the rubber on himself. She bit her lip in anticipation; having been up close and personal with that particular part of him, she knew this was going to be a tight fit. He grinned and rushed back to her, pinning her to the bed.

"Are you sure?" he asked. Madeline's heart swelled at his question. All doubts she had about sleeping with Dean disappeared. Not wanting to embarrass herself, she simply nodded, running her hands over his shoulders. He slipped a hand between them, sliding a finger in her. She sighed and closed her eyes. She felt his lips against her ear and he whispered, "God, you're beautiful." Before she had time to respond, he placed the head of his cock at her entrance and moved his hips forward.

Slowly, ever so slowly, he inched his way inside her, mindful of her comfort. When he was fully seated in her, they both groaned. Kissing her, he pulled back and slammed into her. Madeline gasped loudly and wrapped her legs around him. He continued moving over her as she quickly lost herself to the sensations he was creating. She had never felt this completely fulfilled from sex. His lips were constantly moving over her skin and he was speaking softly to her, a litany of dirty compliments.

"You're so tight and hot, God, you feel incredible. Lift your hips just a little, oh, that's perfect. You're perfect. So beautiful." She felt another climax building, this one starting at her toes. She knew this one was going to be even bigger than the first. His muscles were flexed and his jaw tightened as he kept up his pace. She was groaning now every time he entered her, tilting her hips to draw him in even further. He began moving faster, pushing her closer and closer to the edge.

"Come on Maddy, come for me," he whispered in her ear. That did it. She flew into her orgasm, yelling his name as she did. He growled hers in return; finding his own release as her muscles clenched around him. Both of them panting, Dean rested his forehead against hers. "Wow," he finally said. She giggled happily at his comment.

"I would have to agree," she replied, stretching languidly under him. He climbed off her and walked quickly to the bathroom. Madeline watched sleepily as he disposed of the condom and washed his hands. He crawled back into bed with her, pulling a sheet with him as he did. She had rolled on to her side, and he curled his body around her, wrapping an arm around her waist. He buried his head in her hair and gently kissed her neck.

"Is it okay if I stay for a little while?" he asked. He sounded unsure and slightly nervous, quite the change from the confident sex god he had been minutes before. Madeline smiled, although he couldn't see her, happy that he wasn't as comfortable with this situation as he let on. She snuggled deeper into his arms and sighed contentedly.

"Of course," she said. "I don't have to get up for a couple hours."

"Great," came his answer. Just as she was about to fall asleep, she felt his lips on her shoulder. "I'm glad you changed your mind, Madeline," he whispered, before tightening the hold he had on her.

"So am I, Dean, so am I."


	3. Chapter 3

Title: My Favorite Mistake

Author: Razorbackgal0225

Rating: M—For language, sexual situations and nudity. Three of my favorites

Disclaimer: I don't own any of the characters, cars or situations from Supernatural, but I sure wish I did. Anything you recognize doesn't belong to me, including the title which comes from a Sheryl Crow song. Other songs included in the story are from the group Heart and Pat Benetar. I made no money off anything, I swear!!

Author's Note: This is the wrap-up of the smut story. I hope you enjoyed it. I will be starting work on Catherine's Shack again soon, for those of you who are reading. Thank you so much for the reviews and the readers who have favorite-ed this story, that really means a lot to me, especially since this was my first story of this ilk. Thanks for reading!

* * *

Just like any other Friday morning, she was woken by the smell of coffee wafting into the bedroom. Unlike any other Friday morning, there was a heavy, masculine arm draped around her waist and a possessive hand on her breast. She slowly opened her eyes, seeing by the clock that she had about 20 minutes left before she had to get in the shower. She didn't want to spoil what had turned out to be one of the best nights ever. She closed her eyes and absorbed more of the warmth coming from the body behind her. She was about 2 minutes away from falling back asleep when he spoke. 

"Is that coffee I smell?" his voice was rough with sleep and slightly muffled, as his head was buried in her pillow. She nodded in response and rolled over to face him. She was unprepared for what she saw. Dean last night had been hot and sexy and amazing. Dean this morning was rumpled and adorable and warm, giving her heartstrings a yank. No, she told herself sternly, you can't do that. To her further surprise, he pulled her closer to him. She, in turn, snuggled deeper into his embrace. "I don't want to get up," he said into her hair.

"You have no idea," she mumbled back, wondering why in the world this hadn't happened on a Friday instead of a workday. She dropped a soft kiss on his chest and wrapped her arm around him, seriously considering calling in sick. It wasn't meant to be.

His cell phone began to ring, somewhere from the vicinity of the floor. They both groaned audibly and Dean added some colorful words to that. "Damn it Sam," he complained as he reluctantly threw back the sheet. He kissed her quickly before ordering, "Don't move." He released his hold on her and climbed out of bed. He found his jeans, thrown haphazardly at the foot of her bed and took out his phone. "This is better be important," he said, as a greeting. Madeline watched him from her reclining position. The view was fantastic as he bent over, sorting through the random clothes. He found his boxer briefs and pulled them on with one hand, juggling the phone with the other. Even though he seemed to be listening to whatever his brother was saying, he still heard her rather vocal disapproval of this action. He grinned at her and came back to the bed, sitting next to her. "Are you sure?" he asked into the phone. She propped her head up with one hand, and ran her other over his arm. He grabbed her hand and brought to his mouth, kissing her palm when he did. "Alright, give me a few minutes, and I'll meet you at the motel," he finally said, hanging up the phone after he did.

Uh-oh, she thought to herself, the morning after speech. She began to open her mouth to cut off whatever excuse he had for leaving, but was stopped when he leaned over and kissed her. Generally she was an after-teeth-brushing type of girl, but with him, she threw away that rule, and it landed in the pile of all the other rules she had disobeyed because of him and gorgeous self. Besides, this was most probably good-bye, so she wasn't going to waste the opportunity.

His kiss was soft and thorough, as if he were memorizing the feel of her lips and the taste of her mouth before he left. She was breathless by the time he pulled away. He rested his forehead against hers, as he had the night before, and said quietly, "I'm sorry, Maddy, but I have to go."

Determined to be grown-up about this, she answered simply, "I know," and leaned up for another kiss. This time she was mapping him, running her hands over his face and shoulders, cementing the memory of him in her mind. Too soon, he broke away, brushing his lips across her cheek as he did. Quietly, he stood and began collecting the rest of his clothes, dressing as he did. In just a minute, he was fully clothed again, and she was still wearing only a sheet. Their eyes met and she saw a flash of regret in his, before he smiled and headed to the door.

Realizing she didn't want to leave it this way, she hopped out of bed and grabbed the robe hanging on her bathroom door. Pulling it on, she rushed into the living room and slammed into Dean, who had turned around and was heading back to her room. For a minute, they stared at each other, as an awkward silence settled between them, the first such moment since they had met in the bar. "Do you want some coffee?" she finally, asked, just as he said,

"Could I get some coffee?" The both laughed at each other and themselves. She took his hand and led him into the kitchen. His hands were so manly, she thought as she held his, so strong and capable. Yet another image to store for retrieval at a later date. He sat on a barstool next to the island as she found a travel mug to pour his drink in. She filled the mug, secured the lid and took it to him.

"Here you go," she handed it to him. He took it from her, sitting it on the counter next to him. Then he took her wrist and pulled her between his spread legs. Even sitting, he was able to tuck her head under his chin. He wrapped his arms around her and she did the same. They held each other for a long moment, before he placed a kiss in her hair.

"I'd better go. Sam'll be getting nervous if I'm much later," he explained, as she stepped out of his embrace. She nodded in understanding. He walked to the front door, Madeline following behind him. As he reached the door, he turned to face her again. "Thanks." She shrugged in response. "No, I mean it. I know this isn't the norm for you and…well, thanks for changing your mind." She could tell that while he might be able to talk dirty to a girl, he wasn't as comfortable with talking about feelings. She decided to help him out.

"You're right, this isn't normally me, but I'm really glad I made an exception. I had fun." He smirked at her admission. "Now, don't go getting all cocky or anything, that's not attractive," she kidded him. His expression changed to a genuine smile. He claimed another quick kiss before placing his hand on the handle.

"Bye Maddy," he said, as he opened the door. "Maybe I'll see you around." He walked onto the front porch and down the steps to his car.

She stood in the doorway and watched him climb into old Impala, which seemed to fit him like a glove. He gunned the engine and placed the car in gear before glancing back to her house. She waved at him and he winked in response. She rolled her eyes and he was gone. She didn't take her eyes from the taillights until he had turned out of sight. She sighed out loud and headed back into the house, smiling to herself as she did. She had to admit, this time, the devil on her shoulder had been right. He had definitely not been a mistake.

* * *

She noticed him as soon as he walked in the door. Of course, she had the best view of the entrance, being on stage singing. Generally she didn't notice who came in or went out of the bar as she was concentrating on lyrics, but this guy was different. First of all, she recognized him right away, even though it had been six months since she had seen him. Second, he was alone, no tall brother with him. Last and most importantly, he was brutally hot and he was grinning at her. Her heart skipped a beat, but she managed to keep singing. 

She finished her song, waved to the crowd and helped the band tear down for a few minutes. Then she headed to the bar for her traditional after performance beer. She smiled, but this time it wasn't at the bartender. She had noticed he left his chair the minute she had walked off stage. She took her normal seat and waited. She felt him come and stand beside her, placing a bottle of beer in front of her as he did.

"So," he drawled, "am I going to have to convince you again?" She was laughing when she looked up at him. He winked at her and then leaned down, settling his lips over hers. She couldn't believe how natural this felt, even after all these months. When they separated, she beamed at him.

"I don't think so," she finally answered his question. "Your previous argument was extremely persuasive." He chuckled and kissed her again, then pulled her from the barstool. The angel prepared to cover her eyes and the devil grabbed the massage oil as he took her hand, leading her to the door.


End file.
